N-(hydroxymethyl)benzamide

• ChemBase ID: 9965
• Molecular Formular: C8H9NO2
• Molecular Mass: 151.16256
• Monoisotopic Mass: 151.06332853
• SMILES: N(C(=O)c1ccccc1)CO
• Canonical SMILES: OCNC(=O)c1ccccc1
• InChI: InChI=1S/C8H9NO2/c10-6-9-8(11)7-4-2-1-3-5-7/h1-5,10H,6H2,(H,9,11)
• InChIKey: UOUBPDZUBVJZOQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(hydroxymethyl)benzamide
• IUPAC Traditional name: benzamide, N-(hydroxymethyl)-
• Synonyms: N-(Hydroxymethyl)benzamide; Benzamidomethanol; N-(Hydroxymethyl)benzamide; 苯甲酰氨基甲醇; N-(羟甲基)苯甲酰胺

Database IDs

• CAS Number: 6282-02-6
• EC Number: 228-495-0
• MDL Number: MFCD00014415
• Beilstein Number: 2045129
• PubChem SID: 160973272; 24879528
• PubChem CID: 80493

CALCULATED PROPERTIES

• Acid pKa: 14.2301035
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.4675611
• LogD (pH = 7.4): 0.46756104
• Log P: 0.4675611
• Molar Refractivity: 41.1349 cm^3
• Polarizability: 15.63014 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 102-106°C; 94-96°C; 95-100 °C

Safety Information

• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22-36; 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ≥98.0%; 98%
• Empirical Formula (Hill Notation): C8H9NO2

DETAILS

Sigma Aldrich - 55617

Other Notes
Aminomethylating reagent; employed e.g. for preparing α-amino phosphonic acids1; Preparation of benzamidomethyl protected prodrugs which are fairly stable in physiological medium2

REFERENCES

• For use in the protection of thiols (cf N-(Hydroxymethyl)acetamide, A13820), see: J. Org. Chem., 43, 1270 (1978).